Outlining is an Unnatural Act

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In school, you were probably taught to outline first, then write. That’s good advice at some stages in the process for some writers, but early on you need to understand that outlining is an unnatural act. Outlines are not brain friendly.

Straight Lines Versus Random Connections

An outline goes in a straight line from point A to point B to point C and so on. That’s not how your brain works. Your brain picks up on something, makes a connection to something else and jumps around. You want your brain to make those connections, especially early in the process.

Stories Versus Points

Stories are the way human beings like to communicate best. We tell them to our friends without prompting. When we’re at an event and the speaker says “Let me tell you a story,” we perk up, ready to listen. The internet has become the campfire around which we tell our stories.

Outlines lay out the points you want to make in order. That may be logical, but it’s not natural. Our brain likes to go from stories, filled with concrete detail, to the key points. Outlines go the other way.

Discovering Versus Planning

Human beings prefer to discover things. Outlines lay things out in detailed order, from beginning to end. We’re just not good at that. Think about the last time you planned something new. I bet you had to change your plan when you started putting it into action.

In 1871, Helmut von Moltke said this about military plans: “no plan of operations extends with any certainty beyond the first contact with the main hostile force.” For writing you can think of that as “no outline survives the first draft.”

Organic Writing Versus Engineered Writing

Outlining is engineering for writing, it’s more like building than it is like growing. Organic writing is different.

If you want to write organically, start by writing. Just begin telling your story and see where it goes. You’ll find gaps, and that’s okay. You’ll write some really awful stuff, and that’s okay too.

What will happen if you start writing is that your brain will get everything out that seems to relate to your project. Later, you can go back and change the order, add detail and take things out.

If you’re the sort of person who needs to do a little planning in advance, like I am, block out the stories you want to tell instead of the points you want to make. Then adjust your points to fit your stories.

What If You Can’t Write Without an Outline?

I’m serious. I’ve had clients who must have an outline to write. Many great writers use outlines. If you’re one of those people who needs a detailed outline, hold off making it as long as you can. Get all the benefits of the way your brain naturally works and the way humans naturally communicate and the way the most amazing creations happen. Then outline.

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